3,3-Bis(2-hydroxyethyl)-1-(4-nitrobenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study

Tan, Sang Loon * and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2020) 3,3-Bis(2-hydroxyethyl)-1-(4-nitrobenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study. Acta Crystallographica Section E Crystallographic Communications, 76 (2). pp. 155-161. ISSN 2056-9890

Tiekink Acta Cryst 2020 E76 155.pdf - Accepted Version
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Official URL: http://doi.org/10.1107/S2056989019017328


In the title compound, C12H15N3O5S, a trisubstituted thiourea derivative, the central CN2S chromophore is almost planar (r.m.s. deviation = 0.018 A˚ ) and the pendant hydroxyethyl groups lie to either side of this plane. While to a first approximation the thione-S and carbonyl-O atoms lie to the same side of the molecule, the S—C—N—C torsion angle of 47.8 (2) indicates a considerable twist. As one of the hydroxyethyl groups is orientated towards the thioamide residue, an intramolecular N—H...O hydrogen bond is formed which leads to an S(7) loop. A further twist in the molecule is indicated by the dihedral angle of 65.87 (7) between the planes through the CN2S chromophore and the 4-nitrobenzene ring. There is a close match between the experimental and gas-phase, geometry-optimized (DFT) molecular structures. In the crystal, O— H...O and O—H...S hydrogen bonds give rise to supramolecular layers propagating in the ab plane. The connections between layers to consolidate the three-dimensional architecture are of the type C—H...O, C—H...S and nitroO...π. The nature of the supramolecular association has been further analysed by a study of the calculated Hirshfeld surfaces, non-covalent interaction plots and computational chemistry, all of which point to the significant influence and energy of stabilization provided by the conventional hydrogen bonds.

Item Type: Article
Uncontrolled Keywords: crystal structure; thiourea; nitro group; hydrogen bonding; Hirshfeld surface analysis; computational chemistry
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Sunway University > School of Engineering and Technology [formerly School of Science and Technology until 2020] > Research Centre for Crystalline Materials moved to SMLS wef 2021
Depositing User: Dr Janaki Sinnasamy
Related URLs:
Date Deposited: 04 Mar 2020 09:45
Last Modified: 12 Oct 2020 07:20
URI: http://eprints.sunway.edu.my/id/eprint/1225

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